Top 5 Defining Moments of Winston Churchill's Career

Descended from the Dukes of Marlborough, the boy who would become the legendary Sir Winston Churchill was born into an affluent aristocratic family. A potent and assertive figure his entire life, Churchill served as a military man and journalist in his 20s, and in 1899, when covering the Boer War, he was made a prisoner of war in Pretoria. Churchill’s reputation had yet to proceed him, but he would make a name for himself on the night December 12th, 1899, when he scaled the fence and made a daring escape through enemy territory. He had made fools of the enemy, and Britain was immediately captivated - a legend was born.

Winston Churchill is known for his unflinching resolve, not his failings. And yet, without this notable failure early in his political career, he might never have grown to become the illustrious orator he’s remembered as today. After returning home from the war, Churchill turned his sights on politics, becoming an MP by the age of 25. On April 22, 1904, he was giving an important and rather radical speech about Trade Unions and the Trade Dispute Bill. Unfortunately, Churchill lost his train of thought mid-sentence and, failing to regain it, thanked the members for listening and sat down defeated. From that point on, he kept detailed notes with him and planned his speeches with care.

Over the years that followed his 1904 speech, Churchill’s reputation only continued to grow, both within the military and in politics - though not always in the positive sense. In separate instances, he was both isolated within the Conservative Party and politically exiled. When, just like he had warned, Germany rearmed and returned as a hostile force however, the once unpopular figure was suddenly essential to the Nation once again. And when Britain’s Prime Minister Neville Chamberlain’s policy of German appeasement failed, Churchill, who had been vocally opposed to this strategy, was named his successor. Though an often controversial figure, the general feeling was that no man was better suited to lead during wartime.

Though Churchill may have been selected for his military mind, war was not a foregone conclusion when he assumed the Premiership. The War Cabinet of Britain met for days on end in May of 1940, and there were those present who wanted to negotiate, an option recently offered by Italy, who wished to serve as a mediator between Britain and Germany. But Churchill would have none of it. Instead, he led the country through war. Many of his greatest speeches would be delivered in the months to follow, including “We Shall Fight on the Beaches,” “Their Finest Hour,” “Blood, Toil, Tears and Sweat” and “The Few.”

Suffice it to say, the war was not easily won, and when Britain had its back against the wall, there are surely those who doubted the decision Churchill made when he chose to fight. But in the end, England and its allies prevailed over Hitler, fascism and the Axis powers, and that victory was in no small part thanks to Churchill’s fearless leadership. They had survived Dunkirk, the Battle of Britain and the Blitz, and on May 8th 1945, now remembered as VE Day, they officially triumphed. When Churchill told the crowds at Whitehall that it was their victory, they reportedly roared back “No - it is yours.”